2-羟基螺[4,5]-癸-1-烯-3-酮 | 122821-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基螺[4,5]-癸-1-烯-3-酮
• 英文名称: 2-hydroxyspiro<4,5>-dec-1-en-3-one
• 英文别名: 2-Hydroxyspiro<4.5>dec-1-en-3-one；3-Hydroxyspiro[4.5]dec-3-en-2-one
• CAS: 122821-50-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: UVSXYAIUCRNYIK-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 2 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羟基螺[4,5]-癸-1-烯-3-酮 在 18-冠醚-6 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 加巴喷丁杂质E 、 1,1-环己基二乙酸 、 (1-formylcyclohexyl)acetic acid
  参考文献：
  名称：

  Superoxide anion radical (02.bul.-) mediated base-catalyzed autoxidation of .alpha.-keto enols

  摘要：

  DOI：

  10.1021/jo00281a031
• 作为产物：
  描述：

  3,4-Dihydroxyspiro<5.5>undecan-3-en-4-one 在 18-冠醚-6 、 碘甲烷 作用下， 以 甲苯 为溶剂， 反应 5.67h， 生成 2-羟基螺[4,5]-癸-1-烯-3-酮
  参考文献：
  名称：

  Reaction of Superoxide with Aci-Reductones

  摘要：

  Three reductones, 2,3-dihydroxy-4,4-diphenyl-2,5-cyclohexadien-1-one(11), 3,4-dihydroxycoumarin (35), and 3,4-dihydroxyspiro[5.5]undecan-3-en-4-one (64), were prepared and subsequently reacted with superoxide anion radical(O-2(.-)), generated from KO2 and 18-crown-6 polyether. The reactions were carried out in aprotic media and quenched with methyl iodide which facilitates the trapping of the various oxyanions formed. While a plethora of products were formed in each case [2-hydroxy-2-methyl-4,4-diphenyl-5-cyclohexene-1,3-dione (17), dimethyl 4,4-diphenylglutaconate (18), methyl 4,4-diphenyl-3-butenoate (19), phenylcinnamaldehyde (20), methyl 3-phenylcinnamate (21), and benzophenone (22) from 11; 3-hydroxy-2-methoxycoumarin (39), 2-carbomethoxy-2-hydroxy-3-coumaranone (40), 2-hydroxy-2-methyl-3-coumaranone (41), methyl o-hydroxyphenylglyoxylate (42), methyl salicylate (43), and catechol (44) from 35; and 2,4-dihydroxyspiro[5.5]undeca-1,4-dien-3-one (66), 2-hydroxyspiro[4.5]dec-1-en-3-one (70), dimethyl 1,1-cyclohexanediacetate (73), and dimethyl alpha-keto-1-[(methoxycarbonyl)methyl]cyclohexane (75) from 64], an overall analysis of the product distribution indicates that the basic elements of the reaction sequence are the same. The first step involves facile deprotonation and the concomitant generation of the reductone monoanion, a process which lends support to the suggestion of Afanas'ev and co-workers (Afanas'ev, I. B.; Grabovetskii, V. V.; Kuprianova, N. S. J. Chem. Sec. Perkin Trans. 2 1987, 281-285). Oxidation of this monoanion yields the corresponding triketone. Of the various options available to this polyketone, superoxide attack at the most electrophilic central carbonyl followed by oxidative cleavage and/or benzylic acid rearrangement are clearly the most prominent. These are followed by a variety of base catalyzed autoxidative processes which are highly dependent on the nature of the substrate.

  DOI：

  10.1021/jo00119a031

文献信息

• FRIMER, ARYEH A.;GILINSKY-SHARON, PESSIA;ALJADEFF, GLADIS;MARKS, VERED;RO+, J. ORG. CHEM., 54,(1989) N0, C. 4866-4872
  作者：FRIMER, ARYEH A.、GILINSKY-SHARON, PESSIA、ALJADEFF, GLADIS、MARKS, VERED、RO+

  DOI：——

  日期：——